4-hydroxy-4-(2'-phenyl-2'-aminoethyl)-thiacyclohexane | 164172-63-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-hydroxy-4-(2'-phenyl-2'-aminoethyl)-thiacyclohexane
• 英文别名: 4-(2-amino-2-phenylethyl)thian-4-ol
• CAS: 164172-63-8
• 化学式: C₁₃H₁₉NOS
• 分子量: 237.366
• InChiKey: AYHQBGPLEPXOOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4-(2'-phenyl-2'-aminoethyl)-thiacyclohexane 以74%的产率得到
  参考文献：
  名称：

  Froehlich J., Fiera L., Sauter F., Feng Y., Ertl P., Monatsh. Chem, 126 (1995) N 1, S 75-84

  摘要：

  DOI：
• 作为产物：
  描述：

  3-phenyl-1-oxa-8-thia-2-azaspiro[4.5]dec-2-ene 以91%的产率得到
  参考文献：
  名称：

  Froehlich J., Fiera L., Sauter F., Feng Y., Ertl P., Monatsh. Chem, 126 (1995) N 1, S 75-84

  摘要：

  DOI：

文献信息

• Regioselectivity of cycloadditions of nitrile oxides and nitrones to 4-methylene-tetrahydrothiopyrane
  作者：J. Fröhlich、L. Fišera、F. Sauter、Y. Feng、P. Ertl

  DOI：10.1007/bf00811759

  日期：1995.1

  The cycloaddition of nitrile oxides and nitrones to 4-methylene-tetrahydrothiopyrane proceeds regioselectively under the formation of spiro-substituted isoxazole derivatives 4 and 9. Semiempirical calculations (AM1) were used to analyze the electronic structure of reactants, energies of products, and activation barriers leading to these products in order to rationalize this exclusive regioselectivity. It was shown that the main factor responsible for the high stereoselectivity of this reaction is not frontier orbital control, but mainly electrostatic and steric interactions. The spiro compounds 4 were cleaved by hydrogenolysis to gamma-amino-alcohols 11, which were recyclized to spiro-oxazines 12 and 13.4 and 9 as well as 12 and 13 are derivatives of novel heterocylic systems.